#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/48/1554864.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1554864
loop_
_publ_author_name
'Dorfner, Walter L.'
'Carroll, Patrick J.'
'Schelter, Eric J.'
_publ_section_title
;
 Substituted quinoline quinones as surrogates for the PQQ cofactor: an
 electrochemical and computational study.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              1850
_journal_page_last               1853
_journal_paper_doi               10.1021/acs.orglett.5b00486
_journal_volume                  17
_journal_year                    2015
_chemical_formula_sum            'C14 H11 N O7'
_chemical_formula_weight         305.24
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      33
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.6933(5)
_cell_length_b                   19.9383(12)
_cell_length_c                   7.6281(4)
_cell_measurement_temperature    100(1)
_cell_volume                     1322.18(13)
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0121
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            22320
_diffrn_reflns_theta_full        25.38
_diffrn_reflns_theta_max         25.38
_diffrn_reflns_theta_min         2.04
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2417
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0229
_refine_ls_R_factor_gt           0.0222
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0411P)²+0.2050P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0602
_refine_ls_wR_factor_ref         0.0607
_reflns_number_gt                2371
_reflns_number_total             2417
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b00486_si_002.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

data name '_atom_site_symetry_multiplicity' was replaced with
'_atom_site_symmetry_multiplicity' as specified in the replacement
file
'/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/lists/replacement-tags.lst'.

Automatic conversion script
Id: cif_correct_tags 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P n a 21   '
_cod_database_code               1554864
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'
'-x, -y, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.62836(13) 0.34449(6) 0.48499(17) 0.0143(3) Uani 1 1 d .
C2 C 0.61606(13) 0.27571(6) 0.45485(17) 0.0161(3) Uani 1 1 d .
H2 H 0.5824 0.2597 0.3469 0.021 Uiso 1 1 calc R
C3 C 0.65451(13) 0.23170(6) 0.58709(17) 0.0153(3) Uani 1 1 d .
C4 C 0.70441(14) 0.25809(6) 0.74835(17) 0.0148(3) Uani 1 1 d .
C5 C 0.74075(13) 0.21572(6) 0.90161(18) 0.0156(2) Uani 1 1 d .
C6 C 0.80617(14) 0.23934(6) 1.04936(17) 0.0176(3) Uani 1 1 d .
H6 H 0.8275 0.2099 1.1408 0.023 Uiso 1 1 calc R
C7 C 0.84373(13) 0.30947(6) 1.06809(17) 0.0169(3) Uani 1 1 d .
C8 C 0.79329(14) 0.35816(6) 0.92095(17) 0.0166(3) Uani 1 1 d .
C9 C 0.71911(14) 0.32801(6) 0.76135(17) 0.0144(3) Uani 1 1 d .
C10 C 0.58598(14) 0.39095(6) 0.33773(18) 0.0163(3) Uani 1 1 d .
C11 C 0.54136(19) 0.50117(7) 0.2464(2) 0.0318(4) Uani 1 1 d .
H11a H 0.6024 0.4944 0.1430 0.048 Uiso 1 1 calc R
H11b H 0.5536 0.5465 0.2864 0.048 Uiso 1 1 calc R
H11c H 0.4351 0.4930 0.2196 0.048 Uiso 1 1 calc R
C12 C 0.65281(14) 0.15799(6) 0.54225(16) 0.0155(3) Uani 1 1 d .
C13 C 0.50356(16) 0.05996(6) 0.52765(19) 0.0235(3) Uani 1 1 d .
H13a H 0.5037 0.0550 0.4025 0.035 Uiso 1 1 calc R
H13b H 0.4092 0.0425 0.5744 0.035 Uiso 1 1 calc R
H13c H 0.5889 0.0358 0.5765 0.035 Uiso 1 1 calc R
C14 C 0.71743(14) 0.10405(6) 1.01497(18) 0.0204(3) Uani 1 1 d .
H14a H 0.8244 0.1005 1.0448 0.031 Uiso 1 1 calc R
H14b H 0.6799 0.0611 0.9778 0.031 Uiso 1 1 calc R
H14c H 0.6604 0.1188 1.1156 0.031 Uiso 1 1 calc R
N1 N 0.67985(11) 0.37062(5) 0.63434(14) 0.0150(2) Uani 1 1 d .
O1 O 0.59152(11) 0.45505(4) 0.38294(12) 0.0220(2) Uani 1 1 d .
O2 O 0.55132(11) 0.37031(4) 0.19395(12) 0.0183(2) Uani 1 1 d .
O3 O 0.51704(10) 0.13057(4) 0.57244(13) 0.0173(2) Uani 1 1 d .
O4 O 0.76201(11) 0.13066(4) 0.47672(15) 0.0240(2) Uani 1 1 d .
O5 O 0.69874(11) 0.15196(4) 0.87451(12) 0.0196(2) Uani 1 1 d .
O6 O 0.91218(11) 0.33239(5) 1.19449(13) 0.0215(2) Uani 1 1 d .
O7 O 0.81955(11) 0.41733(5) 0.93319(12) 0.0223(2) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N1 C1 C2 123.50(12)
N1 C1 C10 118.79(11)
C2 C1 C10 117.67(12)
C3 C2 C1 119.13(12)
C2 C3 C4 118.48(11)
C2 C3 C12 116.86(11)
C4 C3 C12 124.44(11)
C9 C4 C3 117.48(12)
C9 C4 C5 119.53(12)
C3 C4 C5 122.99(11)
O5 C5 C6 125.18(12)
O5 C5 C4 111.26(11)
C6 C5 C4 123.55(11)
C5 C6 C7 121.13(11)
O6 C7 C6 123.41(12)
O6 C7 C8 118.42(11)
C6 C7 C8 118.16(11)
O7 C8 C9 122.38(11)
O7 C8 C7 120.28(11)
C9 C8 C7 117.27(10)
N1 C9 C4 123.94(12)
N1 C9 C8 116.34(11)
C4 C9 C8 119.58(11)
O2 C10 O1 124.99(12)
O2 C10 C1 121.97(11)
O1 C10 C1 113.04(11)
O4 C12 O3 126.15(11)
O4 C12 C3 121.84(11)
O3 C12 C3 111.85(10)
C1 N1 C9 117.33(11)
C10 O1 C11 114.33(11)
C12 O3 C13 115.59(9)
C5 O5 C14 118.86(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.3302(17)
C1 C2 1.3947(17)
C1 C10 1.5019(17)
C2 C3 1.3780(18)
C3 C4 1.4064(18)
C3 C12 1.5091(16)
C4 C9 1.4035(17)
C4 C5 1.4765(18)
C5 O5 1.3388(15)
C5 C6 1.3474(19)
C6 C7 1.4429(17)
C7 O6 1.2217(16)
C7 C8 1.5474(17)
C8 O7 1.2054(15)
C8 C9 1.5030(18)
C9 N1 1.3331(17)
C10 O2 1.2096(17)
C10 O1 1.3245(15)
C11 O1 1.4565(17)
C12 O4 1.2034(16)
C12 O3 1.3210(15)
C13 O3 1.4535(14)
C14 O5 1.4445(15)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 102503454
